Potassium Carbonate → HCID 14995282, compound

HRID 2248877Notes

Reaction equation

HRID 2248877 reaction equation
O.O.O.O.O.[N:6]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH:9]=[CH:8][C:7]=1[CH2:16][O:17][C:18]1[CH:19]=[C:20]([CH:22]=[CH:23][CH:24]=1)[O-:21].[Na+].C(=O)([O-])[O-].[K+].[K+].[C:32]([C:34]1[O:35][C:36]2[CH:42]=[C:41]([CH2:43]Br)[CH:40]=[CH:39][C:37]=2[N:38]=1)#[N:33]>CC(C)=O.CN(C)C=O>[C:32]([C:34]1[O:35][C:36]2[CH:42]=[C:41]([CH2:43][O:21][C:20]3[CH:22]=[CH:23][CH:24]=[C:18]([O:17][CH2:16][C:7]4[CH:8]=[CH:9][C:10]5[C:15](=[CH:14][CH:13]=[CH:12][CH:11]=5)[N:6]=4)[CH:19]=3)[CH:40]=[CH:39][C:37]=2[N:38]=1)#[N:33]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 19994737HCID 19994737, compoundHCID 23684420HCID 23684420, compound

Product 1

HCID 14995282HCID 14995282, compound

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of sodium 3-(2-quinolinylmethyloxy)phenoxide pentahydrate (3.63 g, 10 mmol) in acetone (85 ml) and dimethylformamide (10 ml) at room temperature are added successively potassium carbonate (2.07 g, 15 mmol) and 2-cyano-6-bromomethylbenzoxazole (1.90 g, 8.02 mmol). The resulting solution-suspension is refluxed for 16 hours and concentrated. Water (100 ml) and ethyl acetate (200 ml are added. Extraction with ethyl acetate is followed by washing with water and brine, drying (MgSO4) and evaporation under reduced pressure. The residue is subjected to flash chromatography over silica gel. Elution with 33% ethyl acetate in hexane and concentration of the appropriate fractions provides 2-cyano-6-[3-(2-quinolinylmethyloxy)phenoxymethyl]benzoxazole which is used directly in the next step.

Workup

  1. temperatureThe resulting solution-suspension is refluxed for 16 hours
  2. concentrationconcentrated
  3. additionWater (100 ml) and ethyl acetate (200 ml are added
  4. extractionExtraction with ethyl acetate
  5. washby washing with water and brine
  6. customdrying
  7. custom(MgSO4) and evaporation under reduced pressure
  8. washElution with 33% ethyl acetate in hexane and concentration of the appropriate fractions

Sources & evidence

ORD record
ord-bb0711b0e70f47f589cb1ad4efd9d844
Source dataset
uspto-grants-1991_08
Patent number
US05041453

Reaction notes

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